Document Detail

Synthesis and photodynamic effect of new highly photostable decacationically armed [60]- and [70]fullerene decaiodide monoadducts to target pathogenic bacteria and cancer cells.
MedLine Citation:
PMID:  22512669     Owner:  NLM     Status:  MEDLINE    
Novel water-soluble decacationically armed C(60) and C(70) decaiodide monoadducts, C(60)- and C(70)[>M(C(3)N(6)(+)C(3))(2)], were synthesized, characterized, and applied as photosensitizers and potential nano-PDT agents against pathogenic bacteria and cancer cells. A high number of cationic charges per fullerene cage and H-bonding moieties were designed for rapid binding to the anionic residues displayed on the outer parts of bacterial cell walls. In the presence of a high number of electron-donating iodide anions as parts of quaternary ammonium salts in the arm region, we found that C(70)[>M(C(3)N(6)(+)C(3))(2)] produced more HO(•) than C(60)[>M(C(3)N(6)(+)C(3))(2)], in addition to (1)O(2). This finding offers an explanation of the preferential killing of Gram-positive and Gram-negative bacteria by C(60)[>M(C(3)N(6)(+)C(3))(2)] and C(70)[>M(C(3)N(6)(+)C(3))(2)], respectively. The hypothesis is that (1)O(2) can diffuse more easily into porous cell walls of Gram-positive bacteria to reach sensitive sites, while the less permeable Gram-negative bacterial cell wall needs the more reactive HO(•) to cause real damage.
Min Wang; Liyi Huang; Sulbha K Sharma; Seaho Jeon; Sammaiah Thota; Felipe F Sperandio; Suhasini Nayka; Julie Chang; Michael R Hamblin; Long Y Chiang
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural     Date:  2012-04-26
Journal Detail:
Title:  Journal of medicinal chemistry     Volume:  55     ISSN:  1520-4804     ISO Abbreviation:  J. Med. Chem.     Publication Date:  2012 May 
Date Detail:
Created Date:  2012-05-10     Completed Date:  2012-09-12     Revised Date:  2013-06-26    
Medline Journal Info:
Nlm Unique ID:  9716531     Medline TA:  J Med Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  4274-85     Citation Subset:  IM    
Department of Chemistry, Institute of Nanoscience and Engineering Technology, University of Massachusetts, Lowell, Massachusetts 01854, USA.
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MeSH Terms
Antineoplastic Agents / chemical synthesis,  chemistry,  pharmacology*
Bacteria / drug effects*
Drug Stability
Fullerenes / chemistry,  pharmacology*
HeLa Cells
Iodides / chemical synthesis,  chemistry,  pharmacology*
Magnetic Resonance Spectroscopy
Photochemotherapy / methods*
Photosensitizing Agents / chemical synthesis,  chemistry,  pharmacology*
Quaternary Ammonium Compounds / chemical synthesis,  chemistry,  pharmacology*
Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
Spectrophotometry, Ultraviolet
Grant Support
1R01CA137108/CA/NCI NIH HHS; R01 CA137108/CA/NCI NIH HHS
Reg. No./Substance:
0/Antineoplastic Agents; 0/Fullerenes; 0/Iodides; 0/Photosensitizing Agents; 0/Quaternary Ammonium Compounds

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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